Hydrochloric Acid → 1-(2-Chlorobenzofuran-5-yl)propan-1-one
Reaction equation
[Cl:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]3([CH2:16][CH3:17])OCC[O:12]3)=[CH:7][C:5]=2[CH:6]=1.Cl>CO>[Cl:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11](=[O:12])[CH2:16][CH3:17])=[CH:7][C:5]=2[CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 2-chloro-5-(2-ethyl-1,3-dioxolan-2-yl)benzofuran (250 mg, 1.0 eq) in 15 mL MeOH was added 3 mL 3N HCl (aq) at rt. The reaction was stirred for 30 min at rt, quenched with sat NaHCO3 (aq), and extracted with EtOAc. The extract was washed with brine, dried, concentrated, and purified by column chromatography to give the desired product (140 mg, 68%). 1H NMR (400 MHz, CDCl3) δ 8.15 (d, J=1.6 Hz, 1H), 7.95 (dd, J=8.4 Hz, 1.6 Hz, 1H), 7.48 (d, J=8.8 Hz, 1H), 6.68 (s, 1H), 3.06 (q, J=6.8 Hz, 2H), 1.25 (t, J=6.8 Hz, 3H).